Vulcanized caoutchouc-like substance.



"on man STATES PATENT OFFICE;

FRITZ HOFMANN, CARL COUTELLE, KONRAD DELBR'U'CK, AND KURT MEISENBURG, O1ELBERFELD, GERMANY, ASSIGNOBS TO FARBENFABRIKEN VORM. FRIEDR. BAYER &00., 0F ELBERFELD, GERMANY, A CORPORATION OF GERMANY.

VULCANIZED CAOUTCHOUC-LIKE SUBSTANCE.

No Drawing.

in which at least 2 atoms of H are substituted by methyl-groups, forexample:

cm /CH3 cH-cH, oH-i o Oil-CH (EH-CH3 e ll JJI a ll II CH8 -0H, -cm H 'H-CH3 c-cs cu c-cH, H on -oH -cna u g n .11 pm cm H, on, cH-orn. cm (\CHEIt has now been found that these caoutchouc like substances can bevulcanized, substances being obtained equal to and some even better thanvulcanized natural caoutchouc. These facts could not be foreseen in theexistent state of knowledge with regard to the nature and the processesduring the vulcanizing of caoutchouc. One could not know if the newcaoutchouc-like substances too would 'show the same behavior tovulcanizing agents as the natural caout chouc does. Still less could onepredict, whether the vulcanized products, if they could be obtained atall, would have the same valuable properties of vulcanized caoutchouc.

In order to illustrate our invention the following examples are given,the parts being by weight Example 1: 5 parts of the caoutchouc likesubstance obtained by the polymerization of beta-gamma-dimethylerythreneare dissolved in 100 parts of benzene. A solution of one part of surfurmono-chlorid (S Cl in 50 parts of carbon disulfid CS is added and themixture is allowed to stand for 1.5 to 2 minutes, and is then pouredinto alcohol. On stirring a substance separates Specification of LettersPatent.

Patented Jan. 13, 1914.

Application filed March 20, 1911. Serial No. 615,665.

which is distinguished from the parent material by being of greatertoughness and of better resistance to different agents. It is grayish incolor and not adhesive.

Example 2: 50 parts of the caoutchouc like substance obtained bypolymerization of beta-gammadimethylerythrene are intimately mixed bymeans of mixing rolls with 15 parts of powdered sulfur. The productshaped from the resulting sheet is then heated in a suitable apparatusfor from o to 6 hours at 150160 C.

Example 3. 100 parts of the product of polymerization obtained fromtetramethylerythrene are carefully worked together with 10 parts ofsublimed sulfur in a mix,- ing apparatus provided with rolls until ahomogeneous mass results. The resulting product is brought into thedesired shape and is then subjected in an iron vulcanizing vessel to theaction e 'f steam under a pressure of 34 atmospheres. After from 1 to 2hours the process is complete.

Instead of the products of polymerization I used in the examples amixture of the caoutchouc like product obtained from the hydrocarbonsmentioned with natural caoutchouc can be used; similarly other methodsin use for vulcanization can also ,be emplo-yed.

The novel vulcanized caoutchouc substances of the present invention formozonids which upon decomposition with water yieldpoly-methyl-substituted derivatives (aldehydes or ketones) of succinicaldehyde,

( I II 0 Thus the vulcanized caoutchouc substance made frombeta-gamma-dimethylerythrene caoutchouc by vulcanization yields amongthe decomposition products of its ozonid with water acetonylacetone.

oHa-ocma -c-om,

or thel/L-dimethyl derivative of succinic aldehyde. Vulcanized mixturesof the novel caoutchouc substances with natural caoutchouc in additionyield levulinic derivatives, particularly levulinic aldehyde, thel-methyl derivative of succinic aldehyde,

We claim 1. As a new product a vulcanized caoutchouc-like substancecomprising the vulcanized caoutchouc-like polymerization product of apoly-substituted erythrene hydrocarbon being a grayish non-adhesivevsubstance containing sulfur and formin ozonids which upon decompositionwith water yield poly-substituted derivatives of succinic aldehyde.

2. As a new product a vulcanized caoutchouc-like substance comprisingthe vulcanized caoutchouc-lilte polymerization roduct of apoly-methyl-substitlited erytiirene hydrocarbon being a grayishnon-adhesive substance containing sulfur and forming ozonids which upondecomposition with water yield poly-methyl substituted derivatives ofsuccinic aldehyde.

3. As a new product a vulcanized caoutchouc-likc substance comprisingthe vulcanized caoutchouc-like polymerization roduct of abeta-gamma-substituted eryt rene hydrocarbon being a grayishnon-adhesive substance containing sulfur and forming ozonids which upondecomposition with water yield disubstituted derivatives of succinicaldehyde.

4. As a new product a vulcanized caoutchouc-like substance comprisingthe vulcanized caoutchouc-like polymerization :prodnot of adimethyl-erythrene hydrocarbon being a grayish non-adhesive substancecontaining sulfur and forming ozonids which upon decomposition withWater yield dimethyl substituted derivatives of succinic aldehyde.

5. As a new product a vulcanized caoutchouc-like substance comprisingthe vulcanized caoutchouc-like polymerization product ofbeta-gamma-dimethyl-erythrene being a grayish non-adhesive substancecontaining sulfur and forming ozonids which upon decomposition withwater yield acetonylacetone.

6. As a new product a vulcanized caoutchouc-like substance comprising avulcanized mixture of natural caoutchouc and the caoutchouc-likepolymerization product of a poly-substituted erythrene hydrocarbon beinga grayish non-adhesive substance containing sulfur and forming ozonidswhich linic aldehyde and poly-substituted deriva tives of succinicaldehyde.

7. As a new product a vulcanized caoutchouc-like substance comprising avulcanized mixture of natural caoutchouc and the caoutchouc-likepolymerization product of a poly-methyl-substituted erythrenehydrocarbon being a grayish non-adhesive substance containing sulfur andforming ozonids which upon decomposition with water yield levulinicaldehyde and polymethyl-substituted derivatives of succinic aldehyde.

8. As a new product a vulcanized caoutchouc-like substance comprising avulcanized mixture of natural caoutchouc and the caoutchouc-likepolymerization product of a beta-gamma-substituted erythrene hydrocarbonbeing a grayish non-adhesive substance containing sulfur and formingozonids which u on decomposition with water yield levu inic aldehyde anddisubstituted derivatives of succinic aldehyde.

9. As a new product a vulcanized caoutchouc-like substance comprising avulcanized mixture of natural caoutchouc and the caoutchouc-likepolymerization product of a di-methyl-substituted erythrene hydrocarbonbeing a grayish non-adhesive substance containing sulfur and formingozonids which upon decomposition with water yield levulinic aldehyde anddimethyl-substituted derivatives of succinic aldehyde.

' 10. As a new product a vulcanized caoutchouc-like substance comprisinga vulcanized mixture of natural caoutchouc and the caoutehouc-likepolymerization product of beta-gamma-dimethyl erythrene being a. grayishnon-adhesive substance containing sulfur and forming ozonids which upondecomposition with water yield levulinic aldehyde and acetonylacetone.

In testimony whereof We have hereunto set our hands in the presence oftwo subscribing witnesses.

FRITZ HOFMANN.

CARL COUTELLE [1,. s.]

KONRAD DELBRUCK. [1,. 5.]

KURT MEISENBURG. [L. s.] Witnesse s:

CHAS. J. WRIGHT, ALFRED HENKEL.

It is hereby certified that in Letters Patent No. 1,084,835, grantedJanuary 13, 1914, upon the application of Fritz Hofmann, Carl Coutelle,Konrad Delbriick, and Kurt Meisenburg, of Elberfeld, Germany, for animprovement "in Vulcanized Caoutchouc-LikeSubstances an error appears inthe printed specification requiring correction as follows: Page 1, lines98 to 100, for the formula and that the said Letters Patent should beread with this correction therein that the same may conform to therecord of the case in the Patent Ofiice.

Signed and sealed this 31st day of March, A. D., 1914.

[SEAL] J. T. NEWTGN,

Acting Commissioner of Patents.

